Positive anymore is recognized as a feature of some dialects of English. However, because positive anymore occurs infrequently in conversational speech, studies have generally relied on grammaticality judgments. This article takes advantage of the massive corpus of speech-like text available on the social media platform Twitter to study productions of positive anymore in American English. More than 80,000 tweets containing anymore were collected over one month from areas around five Midland cities and three non-Midland cities. Tweets were coded for 20 types of negative polarity item (NPI) triggers and for the position of anymore within clauses. Results confirm that, in the context of American regional Englishes, positive anymore is a distinctive feature of the Midland. However, results also show intraregional differences within the Midland, with anymore being produced more frequently in Pittsburgh and less frequently in the western Midland cities of Kansas City and St. Louis. Midland cities also show increased incidence of anymore with several NPI triggers that should license NPIs in all dialects, suggesting that these ostensibly ordinary NPI triggers may affect or be affected by the use of anymore in positive polarity contexts. More generally, this research models ways that productions of positive anymore and other low-frequency linguistic variables might be studied through media like Twitter.